EP0547226B1 - Verfahren zur zersetzung einer organischer halogenverbindung durch oxydation - Google Patents
Verfahren zur zersetzung einer organischer halogenverbindung durch oxydation Download PDFInfo
- Publication number
- EP0547226B1 EP0547226B1 EP92909560A EP92909560A EP0547226B1 EP 0547226 B1 EP0547226 B1 EP 0547226B1 EP 92909560 A EP92909560 A EP 92909560A EP 92909560 A EP92909560 A EP 92909560A EP 0547226 B1 EP0547226 B1 EP 0547226B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- catalyst
- molding
- component
- oxidative decomposition
- oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 28
- 150000002896 organic halogen compounds Chemical group 0.000 title claims description 22
- 238000006864 oxidative decomposition reaction Methods 0.000 title claims description 21
- 239000003054 catalyst Substances 0.000 claims description 71
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 33
- 239000002912 waste gas Substances 0.000 claims description 22
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 150000002739 metals Chemical class 0.000 claims description 16
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 239000002131 composite material Substances 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 229910052719 titanium Inorganic materials 0.000 claims description 9
- 229910052737 gold Inorganic materials 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 229910052748 manganese Inorganic materials 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- 229910052684 Cerium Inorganic materials 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 238000000465 moulding Methods 0.000 description 39
- 239000007789 gas Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 17
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 16
- 229940117389 dichlorobenzene Drugs 0.000 description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000010936 titanium Substances 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- QPFMBZIOSGYJDE-UHFFFAOYSA-N acetylene tetrachloride Natural products ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 8
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001354 calcination Methods 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000010948 rhodium Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 4
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- -1 and Zr Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- QPFMBZIOSGYJDE-ZDOIIHCHSA-N 1,1,2,2-tetrachloroethane Chemical group Cl[13CH](Cl)[13CH](Cl)Cl QPFMBZIOSGYJDE-ZDOIIHCHSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052878 cordierite Inorganic materials 0.000 description 2
- XAYGUHUYDMLJJV-UHFFFAOYSA-Z decaazanium;dioxido(dioxo)tungsten;hydron;trioxotungsten Chemical compound [H+].[H+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O XAYGUHUYDMLJJV-UHFFFAOYSA-Z 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003609 titanium compounds Chemical class 0.000 description 2
- 229910000349 titanium oxysulfate Inorganic materials 0.000 description 2
- PMTRSEDNJGMXLN-UHFFFAOYSA-N titanium zirconium Chemical compound [Ti].[Zr] PMTRSEDNJGMXLN-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- 150000003755 zirconium compounds Chemical class 0.000 description 2
- OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Chemical compound [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 229910010298 TiOSO4 Inorganic materials 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910003130 ZrOCl2·8H2O Inorganic materials 0.000 description 1
- TWWPCKXWXDAZOR-UHFFFAOYSA-N [Zr].[Ti].[Si] Chemical compound [Zr].[Ti].[Si] TWWPCKXWXDAZOR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011218 binary composite Substances 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- VCJZTATVUDMNLU-UHFFFAOYSA-N dibromomethylbenzene Chemical compound BrC(Br)C1=CC=CC=C1 VCJZTATVUDMNLU-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- BBJSDUUHGVDNKL-UHFFFAOYSA-J oxalate;titanium(4+) Chemical compound [Ti+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O BBJSDUUHGVDNKL-UHFFFAOYSA-J 0.000 description 1
- DAWBXZHBYOYVLB-UHFFFAOYSA-J oxalate;zirconium(4+) Chemical compound [Zr+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O DAWBXZHBYOYVLB-UHFFFAOYSA-J 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HEHINIICWNIGNO-UHFFFAOYSA-N oxosilicon;titanium Chemical compound [Ti].[Si]=O HEHINIICWNIGNO-UHFFFAOYSA-N 0.000 description 1
- KADRTWZQWGIUGO-UHFFFAOYSA-L oxotitanium(2+);sulfate Chemical compound [Ti+2]=O.[O-]S([O-])(=O)=O KADRTWZQWGIUGO-UHFFFAOYSA-L 0.000 description 1
- JSFFXTBMRGAPEX-UHFFFAOYSA-N oxygen(2-) silicon(4+) titanium(4+) zirconium(4+) Chemical compound [Si+4].[O-2].[Zr+4].[Ti+4].[O-2].[O-2].[O-2].[O-2].[O-2] JSFFXTBMRGAPEX-UHFFFAOYSA-N 0.000 description 1
- ZARVOZCHNMQIBL-UHFFFAOYSA-N oxygen(2-) titanium(4+) zirconium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[Ti+4].[Zr+4] ZARVOZCHNMQIBL-UHFFFAOYSA-N 0.000 description 1
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BCWYYHBWCZYDNB-UHFFFAOYSA-N propan-2-ol;zirconium Chemical compound [Zr].CC(C)O.CC(C)O.CC(C)O.CC(C)O BCWYYHBWCZYDNB-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000011206 ternary composite Substances 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- 229910000348 titanium sulfate Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/86—Catalytic processes
- B01D53/8659—Removing halogens or halogen compounds
- B01D53/8662—Organic halogen compounds
Definitions
- the present invention relates to a method for disposing by oxidative decomposition of organohalogen compounds contained in waste gas coming from incinerators, cleaning, and many other processes. More particularly, the present invention relates to a method for disposing by oxidative decomposition of organohalogen compounds while preventing the formation of carbon monoxide by oxidative decomposition and removing organohalogen compounds together with nitrogen oxides and carbon monoxide contained in waste gas.
- WO91/04780 discloses a process for reducing the emission of organic compounds produced by incomplete combustion.
- US-A-4 221 768 teaches a catalyst for selective removal of nitrogen oxides from exhaust and waste gases.
- the present invention was completed to address the above-mentioned problems. It is an object of the present invention to provide a method for efficiently disposing of organohalogen compounds together with nitrogen oxides and carbon monoxide contained in waste gas by oxidative decomposition at low temperatures without the formation of toxic chlorine gas.
- the gist of the present invention resides in a method for disposing of organohalogen compounds by oxidative decomposition, said method being characterized in that a catalyst is used at a temperature between 150-600°C for the oxidative decomposition, said catalyst containing component A and component B: said component A being a composite oxide of two or more metals selected from Si, Ti and Zr, and said component B being an oxide of one or more metals selected from V, Mo, Sn, Ce, and W, and further characterized in that waste gas is incorporated with ammonia gas to facilitate the removal of organohalogen compounds together with nitrogen oxide contained in the waste gas.
- the catalyst may additionally contain a catalyst component C, which is one or more metals selected from Cr, Mn, Fe, Cu. Ru, Rh, Pd. Pt, and Au or an oxide of one or more metals selected from Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt and Au.
- a catalyst component C which is one or more metals selected from Cr, Mn, Fe, Cu. Ru, Rh, Pd. Pt, and Au or an oxide of one or more metals selected from Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt and Au.
- the additional catalyst component C prevents the formation of carbon monoxide. Moreover, with the ammonia added to waste gas, it is possible to remove nitrogen oxides simultaneously with oxidative decomposition of organohalogen compounds and carbon monoxide contained in waste gas.
- the present inventors found that it is possible to perform efficient oxidative decomposition on organohalogen compounds at low temperatures (150-600°C) by the use of a catalyst containing component A, which is a composite oxide of two or more metals selected from the group consisting of Si, Ti, and Zr, and component B, which is an oxide of one or more metals selected from the group consisting of V, Mo, Sn, Ce, and W.
- component A which is a composite oxide of two or more metals selected from the group consisting of Si, Ti, and Zr
- component B which is an oxide of one or more metals selected from the group consisting of V, Mo, Sn, Ce, and W.
- the present inventors also found that it is possible to minimize the formation of carbon monoxide if said catalyst further contains component C, which is one or more metals selected from Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt, and Au or an oxide of one or more metals selected from Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt and Au.
- component C is one or more metals selected from Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt, and Au or an oxide of one or more metals selected from Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt and Au.
- the method of the present invention permits the oxidative decomposition of organohalogen compounds and carbon monoxide as well as the removal of nitrogen oxides due to ammonia gas added to the waste gas.
- the organohalogen compounds referred to in the present invention are defined as any organic compound having at least one halogen atom in the molecule. They include aliphatic organochlorine compounds (such as methyl chloride, ethyl chloride, dichloroethylene, and vinyl chloride), aliphatic organobromine compounds (such as methyl bromide, methylene bromide, ethylene bromide, and vinyl bromide), aromatic organochlorine compounds (such as monochlorobenzene and dichlorobenzene), aromatic organobromine compounds (such as benzyl bromide and benzylidene bromide), toxic organochlorine compounds (such as polydibenzodioxin chloride and polybenzofuran chloride), and flon gas (such as trichlorofluoromethane and dichlorodifluoromethane).
- aliphatic organochlorine compounds such as methyl chloride, ethyl chloride, dichloroethylene, and vinyl chloride
- the method of the present invention may also be used to dispose of waste gas coming from uncatalyzed combustion of solid organochlorine compounds such as PCB and 2,4,5-trichlorophenoxyacetic acid.
- the oxidative decomposition according to the present invention may be accomplished by the use of air or oxygen-enriched air so long as it contains sufficient oxygen to oxidize organohalogen compounds, thereby converting carbon therein into CO 2 and converting halogens into HCl, HBr, HF, and the like.
- the catalyst component A used in the present invention should be a composite oxide of at least two or more metals selected from the group consisting of Si, Ti, and Zr.
- the composite oxide include binary ones (such as titanium-silicon oxide and titanium-zirconium oxide) and ternary ones (such as titanium-silicon-zirconium oxide).
- binary and ternary composite oxides have a larger surface area than the unitary oxide; therefore, they are highly active and effectively disperse the catalyst components B and C for oxidative decomposition. In addition, they are immune to acidic gases such as HCl and SO x contained in waste gas for disposal and hence remain active for a long period of time.
- the catalyst used in the present invention should preferably be composed of 70-95 wt% of catalyst component A (as oxide), 0.1-20 wt% of catalyst component B, and 0.01-25 wt% of catalyst component C.
- Catalyst component B in excess of 20 wt% will lower the strength or the catalyst and shortens the catalyst life.
- Catalyst component B less than 0.1 wt% is not enough for complete decomposition of organohalogen compounds. Therefore, the preferred amount of catalyst component B ranges from 0.1 to 20 wt%.
- Catalyst component C in excess of 25 wt% will raise the catalyst cost.
- Catalyst component C less than 0.01 wt% will permit the formation of carbon dioxide. Therefore, the preferred amount of catalyst component C ranges from 0.01 to 25 wt.
- the catalytic decomposition evolves HCl, HF, HBr, etc., which can be easily removed by any known method such as alkali washing.
- a composite oxide of titanium-silicon, titanium-zirconium, or titanium-silicon-zirconium is mixed with an aqueous solution containing catalyst component B (such as V and W) or oxide powder, molding auxiliary, and an adequate amount of water, and the mixture is molded into a honeycomb by extrusion.
- catalyst component B such as V and W
- the molding is dried at 50-120°C and then calcined at 400-600°C, preferably 430-550°C, for 1-10 hours, preferably 2-6 hours, in an air stream.
- Catalyst component C is supported on the thus obtained molding.
- Catalyst component C is a noble metal such as Ru, Rh, Pd, Pt, and Au, or a metal such as Cr, Mn, Fe, and Cu in the form of simple substance or oxide. In this way there is obtained the desired catalyst.
- the catalyst component C is preferably selected from Ru, Rh, Pd, Pt and Au; among these Au is most preferred
- the method for causing the molding to support catalyst component C is by dipping the molding in an aqueous solution of catalyst component C at room temperature for 1-5 minutes, followed by drying at 30-200°C, preferably 70-170°C, and calcining in air at 300-700°C, preferably 400-600°C.
- the catalyst may take any other forms than honeycomb. For example, it may be in the form of column, cylinder, plate, ribbon, corrugated board, pipe, toroid, grating, or the like.
- the catalyst may also be prepared by coating a carrier (molded from cordierite or mullite) with a slurry of catalyst components A and B and then impregnating the coated carrier with catalyst C.
- Metals used in the preparation of the catalyst of the present invention may be obtained from the following raw materials.
- Silicon may be obtained from colloidal silica, water glass, silicon tetrachloride, and ethyl silicate.
- Titanium may be obtained from inorganic titanium compounds (such as titanium chloride, titanium hydroxide, and titanium sulfate) and organic titanium compounds (such as titanium oxalate and tetraisopropyl titanate).
- Zirconium may be obtained from inorganic zirconium compounds (such as zirconium chloride, zirconium oxychloride, and zirconium nitrate) and organic zirconium compounds (such as zirconium oxalate and tetraisopropyl zirconate).
- the starting material for catalyst component B may be in the form of oxide, hydroxide, inorganic salt, or organic salt, which include ammonium salts, oxalates, sulfates, and halides.
- the starting material for catalyst component C may be in the form of chloride, nitrate, organic salt, chloro-noble metal-acid, or copper compound.
- the oxidative decomposition according to the present invention may be accomplished in any reactor, such as fixed-bed reactor, moving-bed reactor, and fluidized-bed reactor.
- any reactor such as fixed-bed reactor, moving-bed reactor, and fluidized-bed reactor.
- the method of the present invention is used to dispose of organohalogen compounds contained in waste gas coming from incinerators, it is desirable to use the catalyst in honeycomb form so that the opening can be adjusted according to the amount of dust to prevent the catalyst layer from being clogged.
- the reaction temperature should be in the range of 150-600°C. Reactions below 150°C do not permit efficient decomposition; and reaction above 600°C needs more fuel.
- a composite oxide of titanium and silicon was prepared in the following manner. First, a titanium source (in the form of aqueous solution) was prepared from titanyl sulfate and sulfuric acid in a ratio given below. TiOSO 4 (as TiO 2 ) 250 g/L Total H 2 SO 4 1100 g/L
- This aqueous solution (153 liters) was diluted with 300 liters of water.
- the diluted titanium-containing solution was slowly added dropwise with stirring to an ammonium solution for gel coprecipitation.
- the ammonium solution was prepared by adding to 400 liters of water 286 liters of ammonia water (25% NH 3 ) and 24 kg of Snowtex NCS-30 (silica sol containing about 30 wt% SiO 2 , made by Nissan Chemical Industries, Ltd.) After standing for 15 hours, the gel precipitates (of titanium-silicon composite oxide) were filtered off, washed with water, and dried at 200°C for 10 hours.
- TS-1 was made into a molding in the following manner.
- the catalyst was cut into small pieces, each measuring 23 mm square (6 ⁇ 6 cells) and 300 mm long. They were charged into the reactor, through which 1,1,2,2-tetrachloroethane, dichlorobenzene, and flon 113 were passed for decomposition under the same conditions as in Reference Example 1. The results are shown in Table 2. In all the cases, no chlorine gas was detected in the decomposed gas.
- the catalyst was cut into small pieces, each measuring 23 mm square (6 ⁇ 6 cells) and 300 mm long. They were charged into the reactor, through which 1,1,2,2-tetrachloroethane, dichlorobenzene, and flon 113 were passed for decomposition under the same conditions as Reference Example 1. The results are shown in Table 3. In all the cases, no chlorine gas was detected in the decomposed gas.
- This molding is in the form of honeycomb shaped molding, measuring 80 mm square and 350 mm long, with an opening of 3.0 mm and a wall thickness of 0.7 mm.
- the molding was dipped in 3.0 liters of aqueous solution containing 170 g of chromium nitrate [Cr(NO 3 ) 3 ⁇ 9H 2 O] for 1 minute. Then the molding was dried at 100°C and calcined in an air stream at 500°C for 2 hours.
- the thus obtained catalyst was found to support Cr 2 O 3 in an amount of 0.38 wt%.
- the catalyst was cut into small pieces, each measuring 23 mm square (6 ⁇ 6 cells) and 300 mm long. They were charged into the reactor, through which dichlorobenzene was passed for decomposition under the same conditions as in Reference Example 1. The results are shown in Table 4. In all the cases, no chlorine gas was detected in the decomposed gas.
- a molding of the same size and composition as that in Reference Example 4 was prepared.
- the molding was dipped in 3.0 liters of aqueous solution containing 1370 g of manganese nitrate [Mn(NO 3 ) 2 ⁇ 6H 2 O] for 1 minute.
- the molding was dried at 100°C and calcined in an air stream at 500°C for 2 hours.
- the thus obtained catalyst was found to carry MnO 2 in an amount of 5 wt%.
- the catalyst was used for decomposition of dichlorobenzene in the same manner as Reference Example 4. The results are shown in Table 4. In all the cases, no chlorine gas was detected in the decomposed gas.
- a molding of the same size and composition as that in Reference Example 4 was prepared.
- the molding was dipped in 3.0 liters of aqueous solution containing 1270 g of copper nitrate [Cu(NO 3 ) 2 ⁇ 3H 2 O] for 1 minute.
- the molding was dried at 120°C and calcined in an air stream at 500°C for 2 hours.
- the thus obtained catalyst was found to support CuO in an amount of 5 wt%.
- the catalyst was used for decomposition of dichlorobenzene in the same manner as in Reference Example 4. The results are shown in Table 4. In all the cases, no chlorine gas was detected in the decomposed gas.
- a molding of the same size and composition as that in Reference Example 4 was prepared.
- the molding was dipped in 3.0 liters of aqueous solution containing 22 g (as Pd) of palladium nitrate. Then the molding was dried at 100°C and calcined in an air stream at 500°C for 2 hours. The thus obtained catalyst was found to support Pd in an amount of 0.25 wt%.
- the catalyst was cut into small pieces, each measuring 23 mm square (6 ⁇ 6 cells) and 300 mm long. They were charged into the reactor, through which nitrogen monoxide, carbon monoxide, dichlorobenzene, and SO 2 -containing gas were passed simultaneously for decomposition under the following conditions. (The gas mixture contains NH 3 as a reducing agent.)
- the gas mixture contains NH 3 as a reducing agent.
- 1. Gas composition Dichlorobenzene 30 ppm v/v NO 300 ppm v/v NH 3 300 ppm v/v CO 1.0 vol% SO 2 100 ppm v/v H 2 O 10 vol% Air balance 2. Space velocity 2000 h -1 3. Reaction temperature 200, 250°C The results are shown in Table 5.
- This composite oxide powder is designated as TZ-1 hereinafter.
- This molding is in the form of honeycomb shaped molding, measuring 80 mm square and 350 mm long, with an opening of 3.0 mm and a wall thickness of 0.7 mm.
- This molding was dipped in 3 liters of aqueous solution of platinum chloride (containing 11.0 g of Pt) for 1 minute. The dipped molding was dried in air at 120°C and calcined in an air stream at 450°C for 2 hours. Thus there was obtained the desired catalyst.
- the catalyst was found to support Pt in an amount of 0.1 wt%.
- a cordierite honeycomb (having 3-mm square holes) was coated with ⁇ -alumina powder, followed by drying and calcining. Pt was supported on the resulting catalyst carrier by the chemical adsorption method, followed by drying at 100°C and calcining in an air stream at 450°C for 2 hours. Thus there was obtained a comparative catalyst, which was found to support Pt in an amount of 0.25 wt%.
- This comparative catalyst was tested in the same manner and under the same conditions as in Reference Example 1 for the decomposition of 1,1,2,2-tetrachloroethane and dichlorobenzene. The results are shown in Table 7.
- a mixture was made from 10 g of commercial TiO 2 powder (having a BET specific surface area of 30 m 2 /g) and 1.5 kg of water.
- the mixture was extrusion-molded into a honeycomb shaped molding, measuring 80 mm square and 350 mm long, with an opening of 3.0 mm and a wall thickness of 0.7 mm.
- the molding was dried at 60°C and then calcined in an air stream at 450°C for 5 hours.
- the thus obtained molding was dipped in 3 liters of aqueous solution of platinum chloride (containing 14 g of Pt) for 1 minute, followed by drying at 100°C and calcining in an air stream at 450°C for 5 hour.
- the present invention provides a method for efficiently disposing, by oxidative decomposition at low temperatures, of organohalogen compounds contained in waste gas, without forming carbon monoxide and halogen gas.
- the method permits the simultaneous removal of organohalogen compounds together with nitrogen oxide and carbon monoxide from waste gas.
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Claims (3)
- Verfahren zur Entsorgung von in Abgasen enthaltenen organischen Halogenverbindungen durch oxidativen Abbau, um sie unschädlich zu machen, wobei das Verfahren dadurch gekennzeichnet ist, daß ein Katalysator bei einer Temperatur zwischen 150 und 600 °C für den oxidativen Abbau verwendet wird, wobei der Katalysator eine Komponente A und eine Komponente B enthält, wobei Komponente A ein Verbundoxid von zwei oder mehr aus Si, Ti und Zr ausgewählten Metallen ist und Komponente B ein Oxid von einem oder mehreren aus V, Mo, Sn, Ce und W ausgewählten Metallen ist, und das Verfahren weiterhin dadurch gekennzeichnet ist, daß in das Abgas Ammoniakgas eingebracht wird, um das Entfernen von im Abgas zusammen mit Stickoxid enthaltenen organischen Halogenverbindungen zu erleichtern.
- Verfahren zur Entsorgung von in Abgasen enthaltenen organischen Halogenverbindungen durch oxidativen Abbau, um sie unschädlich zu machen, wobei das Verfahren dadurch gekennzeichnet ist, daß ein Katalysator bei einer Temperatur zwischen 150 und 600 °C für den oxidativen Abbau verwendet wird, wobei der Katalysator eine Komponente A und eine Komponente B enthält, wobei Komponente A ein Verbundoxid von zwei oder mehr aus Si, Ti und Zr ausgewählten Metallen ist und Komponente B ein Oxid von einem oder mehreren aus V, Mo, Sn, Ce und W ausgewählten Metallen ist, und das Verfahren weiterhin dadurch gekennzeichnet ist, daß in das Abgas Ammoniakgas eingebracht wird, um das Entfernen von im Abgas zusammen mit Stickoxid und Kohlenmonoxid enthaltenen organischen Halogenverbindungen zu erleichtern.
- Verfahren zur Entsorgung von organischen Halogenverbindungen durch oxidativen Abbau nach Anspruch 1 oder 2 und zum Verhindern der Bildung von CO, wobei der Katalysator weiterhin Komponente C enthält, die ein oder mehrere aus Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt und Au ausgewählte Metalle ist oder ein Oxid von einem oder mehreren aus Cr, Mn, Fe, Cu, Ru, Rh, Pd, Pt und Au ausgewählten Metallen ist.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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JP12846491 | 1991-04-30 | ||
JP12846491 | 1991-04-30 | ||
JP128464/91 | 1991-04-30 | ||
PCT/JP1992/000552 WO1992019366A1 (en) | 1991-04-30 | 1992-04-27 | Method of oxidative decomposition of organic halogen compound |
Publications (3)
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EP0547226A1 EP0547226A1 (de) | 1993-06-23 |
EP0547226A4 EP0547226A4 (en) | 1993-12-29 |
EP0547226B1 true EP0547226B1 (de) | 2000-07-19 |
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EP92909560A Expired - Lifetime EP0547226B1 (de) | 1991-04-30 | 1992-04-27 | Verfahren zur zersetzung einer organischer halogenverbindung durch oxydation |
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US (1) | US5430230A (de) |
EP (1) | EP0547226B1 (de) |
DE (1) | DE69231273T2 (de) |
WO (1) | WO1992019366A1 (de) |
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JPS60220148A (ja) * | 1984-04-17 | 1985-11-02 | Nippon Shokubai Kagaku Kogyo Co Ltd | ハニカム型脱臭触媒 |
JP2518292B2 (ja) * | 1987-07-08 | 1996-07-24 | 日立電線株式会社 | 油井用電線・ケ−ブル |
JP2602337B2 (ja) * | 1989-01-09 | 1997-04-23 | 株式会社日本触媒 | 有機塩素化合物の分解燃焼処理方法 |
US4957717A (en) * | 1989-01-09 | 1990-09-18 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Method of disposal of organic chlorine compounds by combustion |
JP2976041B2 (ja) * | 1989-03-06 | 1999-11-10 | 工業技術院長 | 有機ハロゲン化物の除去方法 |
DE3908740A1 (de) * | 1989-03-17 | 1990-11-29 | Didier Werke Ag | Verfahren zur entfernung oder verminderung von halogenierten aromaten aus abgasen von verbrennungsanlagen fuer muell oder sondermuell |
KR950007317B1 (ko) * | 1989-05-01 | 1995-07-10 | 알라이드-시그날 인코포레이티드 | 유기할로겐 화합물들의 촉매 분해방법 및 그에 사용되는 촉매 |
JPH0829220B2 (ja) * | 1989-06-05 | 1996-03-27 | 三菱重工業株式会社 | 排ガス中二酸化硫黄の還元方法 |
JPH07106299B2 (ja) * | 1989-06-08 | 1995-11-15 | 正勝 平岡 | 廃棄物処理方法 |
JPH03106419A (ja) * | 1989-09-20 | 1991-05-07 | Hitachi Ltd | フロン含有ガスの処理方法及びフロン分解用触媒 |
HUT60937A (en) * | 1989-10-06 | 1992-11-30 | Babcock Anlagen Ag | Method for separating orgqnic combustion products originating because of imperfect firing particularly from the exhaust gas of burning apparatus |
JPH03249920A (ja) * | 1990-02-27 | 1991-11-07 | Mitsubishi Heavy Ind Ltd | フルオロカーボンガスの分解方法 |
JPH0714459B2 (ja) * | 1990-09-06 | 1995-02-22 | 正勝 平岡 | 排ガスの処理方法 |
-
1992
- 1992-04-27 US US07/962,590 patent/US5430230A/en not_active Expired - Fee Related
- 1992-04-27 WO PCT/JP1992/000552 patent/WO1992019366A1/ja active IP Right Grant
- 1992-04-27 DE DE69231273T patent/DE69231273T2/de not_active Expired - Fee Related
- 1992-04-27 EP EP92909560A patent/EP0547226B1/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0547226A1 (de) | 1993-06-23 |
DE69231273T2 (de) | 2001-03-15 |
US5430230A (en) | 1995-07-04 |
EP0547226A4 (en) | 1993-12-29 |
DE69231273D1 (de) | 2000-08-24 |
WO1992019366A1 (en) | 1992-11-12 |
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